Compounds, transition metal complex hydroformylation catalyst precuror compositions comprising such compounds, and hydroformylation processes

Abstract

The present disclosure relates generally to compounds, to transition metal complex hydroformylation catalytic precursor compositions, and to processes for separating one or more heavies from a hydroformylation reaction product fluid in hydroformylation processes comprising a metal-monophosphite ligand complex catalyst. In one aspect, the present disclosure relates to a compound of the following formula (I): (I) wherein R1-R5 are the same or different and are H or an alkyl moiety, wherein R6 is H, alkyl, aryl, O—R7, —N(R8)2 and O(CH2CH2)yOR8 moieties, wherein R7 is an alkyl or an aryl moiety, and wherein R8 is H, alkyl, or aryl moieties.

1 . A compound of the following formula: 
       
         
           
           
               
               
           
         
         wherein R 1 -R 5  are the same or different and are H or an alkyl moiety, wherein R 6  is H, alkyl, aryl, O—R 7 , —N(R 8 ) 2  and O(CH 2 CH 2 ) y OR 8  moieties, wherein R 7  is an alkyl or an aryl moiety, and wherein R 8  is H, alkyl, or aryl moieties. 
       
     
     
         2 . A transition metal complex hydroformylation catalytic precursor composition comprising of a solubilized Group VIII transition metal-monophosphite complex, an organic solvent, and free monophosphite ligand, wherein the monophosphite ligand of the metal-monophosphite complex and the free monophosphite ligand are each a compound according to  claim 1 . 
     
     
         3 . The transition metal complex hydroformylation catalytic precursor composition of  claim 2 , wherein the monophosphite ligand of the metal-monophosphite complex and the free monophosphite ligand are the same compound according to  claim 1 . 
     
     
         4 . A process for separating one or more heavies from a hydroformylation reaction product fluid comprising a metal-monophosphite ligand complex catalyst, optionally free monophosphite ligand, one or more aldehyde products, and heavies, the process comprising:
 (a) hydroformylating a C 6  to C 40  mono-olefin with the metal-monophosphite ligand complex catalyst and optionally free monophosphite ligand in a reaction zone to provide a hydroformylation reaction product fluid, wherein the monophosphite ligand in the metal-monophosphite ligand complex catalyst comprises a compound according to  claim 1 ;   (b) removing a portion of the hydroformylation reaction product fluid from the reaction zone and transferring the portion to a product/catalyst separation zone wherein a portion of the aldehyde products are vaporized as an overhead stream and wherein a non-volatilized catalyst fluid comprising the metal-monophosphite ligand complex catalyst is recovered as a bottoms stream;   (c) mixing at least a portion of the bottoms stream obtained in step (b) in the presence of a nonpolar solvent and a polar solvent to obtain, by phase separation, two phases: a first phase comprising the polar solvent, the metal-monophosphite ligand complex catalyst and optionally free monophosphite ligand, and a second phase comprising the non-polar solvent, a portion of the heavies, and at least a portion of the remaining aldehyde products; and   (d) recovering said metal-monophosphite ligand complex catalyst and at least a portion of any free monophosite ligand from the first phase and returning the recovered metal-monphosphite ligand complex catalyst and any recovered free monophosphite ligand to the reaction zone.   
     
     
         5 . The process of  claim 4 , wherein the recovered metal-monophosphite ligand complex catalyst and any recovered free monophosphite ligand from step (d) can be used in the reaction zone without further treatment. 
     
     
         6 . The process of  claim 4  wherein the polar solvent present in step (d) is removed from the first phase prior to the recovered metal-monophosphite ligand complex catalyst and any recovered free monophosphite ligand being returned to the reaction zone. 
     
     
         7 . The process of  claim 4 , wherein the non-polar solvent is distilled from the second phase in step (d) and at least partially recycled. 
     
     
         8 . The process of  claim 4 , wherein the non-polar solvent comprises a C 6 -C 40  mono-olefin and is the same as the mono-olefin being hydroformylated in step (a). 
     
     
         9 . The process of  claim 4 , wherein the non-polar solvent comprises unreacted mono-olefin that is recovered from the overhead stream in step (b). 
     
     
         10 . A hydroformylation process for producing aldehydes, the process comprising:
 reacting an olefinically unsaturated compound selected from the group consisting of alpha-olefins containing from 6 to 40 carbon atoms, internal olefins containing from 6 to 40 carbon atoms, and mixtures of such alpha and internal olefins with carbon monoxide and hydrogen in a reaction zone in the presence of a rhodium-monophosphite complex catalyst consisting essentially of rhodium complexed with carbon monoxide and at least one monophosphite ligand, wherein the at least one monophosphite ligand is a compound according to  claim 1 .   
     
     
         11 . The process according to  claim 10 , wherein the reaction zone further comprises at least one free monophosphite ligand, wherein the at least one free monophosphite ligand is a compound according to  claim 1 . 
     
     
         12 . The process of  claim 10 , wherein the hydroformylation reaction conditions comprise: a reaction temperature from 50° C. to 120° C., a total gas pressure of hydrogen, carbon monoxide, and olefinically unsaturated organic compound from 1 to 1500 psia, a hydrogen partial pressure from 15 to 200 psia, and a carbon monoxide partial pressure from 10 to 200 psia, and wherein the reaction zone contains from 4 to 200 moles of said monophosphite ligand per mole of rhodium. 
     
     
         13 . The process of  claim 10 , wherein the concentration of rhodium in the reaction zone is 5 to 500 ppmw. 
     
     
         14 . The process of  claim 10 , wherein the second phase comprising non-polar solvent and heavies isolated in step (c) is further processed to recover residual aldehyde product. 
     
     
         15 . The process of  claim 10 , wherein at least a portion of the nonpolar solvent and/or polar solvent used in step (c) is provided with the bottoms stream from step (b).